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Advanced Organic Chemistry: Mass spectrum of hexane

The mass spectrum of hexane

Doc Brown's Chemistry Advanced Level Pre-University Chemistry Revision Study Notes for UK IB KS5 A/AS GCE advanced A level organic chemistry students US K12 grade 11 grade 12 organic chemistry courses involving molecular spectroscopy analysing mass spectra of hexane

mass spectrum of hexane fragmentation pattern of m/z m/e ions for analysis and identification of hexane image diagram doc brown's advanced organic chemistry revision notes 

Hexane C6H14, alkanes structure and naming (c) doc b , alkanes structure and naming (c) doc b , alkanes structure and naming (c) doc b

Interpreting the fragmentation pattern of the mass spectrum of hexane

[M]+ is the molecular ion peak (M) with an m/z of 86 corresponding to [C6H14]+, the original hexane molecule minus an electron, [CH3CH2CH2CH2CH2CH3]+.

The small M+1 peak at m/z 87, corresponds to an ionised hexane molecule with one 13C atom in it i.e. an ionised hexane molecule of formula 13C12C5H14

Identifying the species giving the most prominent peaks (apart from M) in the fragmentation pattern of hexane.

m/z value of [fragment]+ 71 58 57 56 55
[molecular fragment]+ [CH3CH2CH2CH2CH2]+ [C4H10]+ [CH3CH2CH2CH2]+ [C4H8]+ [C4H7]+
m/z value of [fragment]+ 43 42 41 39 29 28 27
[molecular fragment]+ [CH3CH2CH2]+ [C3H6]+ [C3H5]+ [C3H3]+ [CH3CH2]+ [C2H4]+ [C2H3]+

Analysing and explaining the principal ions in the fragmentation pattern of the mass spectrum of hexane

Equations to explain the most abundant ion peaks of hexane

Formation of m/z 71 ion: [CH3CH2CH2CH2CH2CH3]+  ===>  [CH3CH2CH2CH2CH2]+  +  CH3

C-C bond scission in the carbon chain of the molecular ion of hexane

Formation of m/z 57 ion: [CH3CH2CH2CH2CH2CH3]+  ===>  [CH3CH2CH2CH2]+  +  CH2CH3

The m/z 57 ion is the base peak ion, the most abundant and 'stable' ion fragment.

Again, C-C bond scission in the carbon chain of the molecular ion of hexane.

Similarly the m/z 57 ion could be formed by further scission of a shorter ion

e.g.: [CH3CH2CH2CH2CH2]+  ===>  [CH3CH2CH2CH2]+  +  CH2

Formation of m/z 43 ion: [CH3CH2CH2CH2CH2CH3]+  ===>  [CH3CH2CH2]+  +  CH2CH2CH3

Formation of m/z 29 ion: [CH3CH2CH2CH2CH2CH3]+  ===>  [CH3CH2]+  +  CH2CH2CH2CH3


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